Pesticide

ABSTRACT

The present invention provides a composition comprising synergistic amounts of a compound of the formula (I) 
                 
 
wherein X, E, R, A and Z are as defined herein, and at least one fungicidal active compound as defined herein. The compositions of the present invention find use as pesticides.

This application is a divisional application of U.S. Ser. No. 09/911,263filed Jul. 23, 2001, now U.S. Pat. No. 6,423,726, which is a divisionalapplication of U.S. Ser. No. 09/585,227, filed Jun. 1, 2000, now U.S.Pat. No. 6,297,263, which is itself a divisional application of U.S.Ser. No. 08/765,819, filed Jan. 7, 1997, now U.S. Pat. No. 6,114,362,which is a 371 of PCT/EP95/02799, filed Jul. 17, 1995.

FIELD OF THE INVENTION

The present invention relates to pest control compositions which containan active compound combination of certain agonists or antagonists of thenicotinic acetylcholine receptors of insects together with fungicides,their preparation and their use for the control of plant pests.

BACKGROUND OF THE INVENTION

Agonists or antagonists of the nicotinic acetylcholine receptors ofinsects are known, for example from the following publications:

European Published Specifications No. 464 830, 428 941, 425 978, 386565, 383 091, 375 907, 364 844, 315 826, 259 738, 254 859, 235 725, 212600, 192 060, 163 855, 154 178, 136 636, 303 570, 302 833, 306 696, 189972, 455 000, 135 956, 471 372, 302 389; German Published SpecificationsNo. 3 639 877, 3 712 307; Japanese Published Specifications No. 03 220176, 02 207 083, 63 307 857, 63 287 764, 03 246 283, 04 9371, 03 279359, 03 255 072; U.S. Pat. No. 5,034,524, 4,948,798, 4,918,798,4,918,086, 5,039,686, 5,034,404; PCT Applications No. WO 91/17 659,91/4965; French Application No. 2 611 114; Brazilian Application No. 8803 621.

The methods, processes, formulae and definitions described in thesepublications, and also the specific preparations and compounds describedtherein, are expressly referred incorporated herein.

Fungicidal active compounds, such as azole derivatives, aryl benzylethers, benzamides, morpholine compounds and other heterocycles areknown (cf. K. H. Büichel “Pflanzenschutz und Schädlingsbekänpfing [Cropprotection and pest control]”, pages 140 to 153, Georg Thieme-Verlag,Stuttgart 1977, EP-OS (European Published Specification) 0 040 345,DE-OS (German Published Specification) 3 324 010, DE-OS (GermanPublished Specification) 2 201 063, EP-OS (European PublishedSpecification) 0 112 284, EP-OS (European Published Specification) 0 304758, and DD-PS (German Democratic Republic Patent Specification) 140412).

Mixtures of certain nitromethylene derivatives with fungicidal activecompounds and their use as compositions for the control of pests in cropprotection are already known U.S. Pat. No. 4,731,385; JP-OS (JapanesePublished Specifications) 63-68507, 63/68505, 63/72 608, 63/72 609,63/72 610). Mixtures of certain open-chain nitromethylenes andnitroguanidines with fungicides are already known (JP-OS (JapanesePublished Specification) 30 47 106; U.S. Pat. No. 5,181,587).

Mixtures of cyclopropylcarboxamides with certain nitromethylenene ornitroguanidine derivatives are already known (JP-OS (Japanese PublishedSpecification) 3 271 207;

Mixtures of inter alia imidacloprid- and fungicidal active compounds foruse in material protection and against termites, but not for use againstplant-damaging pests, are already known (EP-OS (European PublishedSpecification) (Nit 259)). Mixtures of imidacloprid andazolylmethylcycloalkanes, in particular triticonazole, are known fromEP-OS (European Published Specification) 545 834.

However, nothing is yet known about nitroguanidine derivatives andfungicides other than cyclopropylcarboxamides and triticonazoleinfluencing each other so favourably in over action that, while beingwell tolerated by plants, they can be used with outstanding effect ascompositions for the control of plant pests.

DETAILED DESCRIPTION OF THE INVENTION

The present invention relates to plant pest control compositions whichcontain compounds of the the general formula (I)

in which

-   X represents —CH═ or ═N—,-   E represents an electron-withdrawing radical, in particular nitro or    cyano,-   R represents optionally substituted hetarylalkyl,-   A represents hydrogen, alkyl, or a bifunctional group which is    linked to the radical Z,-   Z represents alkyl, —NH, alkyl, —N(alkyl)₂ or a bifunctional group    which is linked to the radical A,    in mixtures with fungicidal active compounds, excluding    cyclopropylcarboxamide derivatives and azolylmethylcycloalkanes.

Preferably, the invention relates to plant pest control compositionswhich contain compounds of the formula (I) in which the radicals havethe following meaning:

-   X represents ═CH— or ═N—,-   E represents NO₂ or CN,-   R represents hetarylmethyl, hetarylethyl having up to 6 ring atoms    and N, O, S, in particular N, as heteroatoms.

In particular there may be mentioned thienyl, furyl, thiazolyl,imidazolyl, pyridyl, which are optionally substituted.

Preferred examples of substituents are:

-   -   alkyl having preferably 1 to 4, in particular 1 or 2 carbon        atoms, such as methyl, ethyl, n- and i-propyl and n-, i- and        t-butyl; alkoxy having preferably 1 to 4, in particular 1 or 2        carbon atoms, such as methoxy, ethoxy, n- and i-propyloxy and        n-, i- and t-butyloxy; alkylthio having preferably 1 to 4, in        particular 1 or 2 carbon atoms, such as methylthio, ethylthio,        n- and i-propylthio and n-, i- and t-butylthio; haloalkyl having        preferably 1 to 4, in particular 1 or 2 carbon atoms and        preferably 1 to 5, in particular 1 to 3 halogen atoms, wherein        the halogen atoms are identical or different and wherein the        halogen atoms are preferably fluorine, chlorine or bromine, in        particular fluorine, such as trifluoromethyl; hydroxyl; halogen,        preferably fluorine, chlorine, bromine and iodine, in particular        fluorine, chlorine and bromine; cyano; nitro; amino; monoalkyl-        and dialkylamino having preferably 1 to 4, in particular 1 or 2        carbon atoms per alkyl group, such as methylamino,        methylethylamino, n- and i-propylamino and methyl-n-butylamino;

-   A represents hydrogen, C₁₋₄alkyl, in particular methyl or ethyl,

-   Z represents C₁₋₄alkyl, in particular ethyl or methyl,    —NH(C₁₋₄alkyl), —N(C₁₋₄alkyl) or

-   A and Z, form together with the atoms to which they are bonded, form    a saturated or unsaturated heterocyclic ring. The heterocyclic ring    may contain a further 1 or 2 identical or different heteroatoms    and/or heterogroups. Preferably, heteroatoms are oxygen or nitrogen    and heterogroups are N-alkyl, the alkyl of the N-alkyl group    containing preferably 1 to 4, in particular 1 or 2 carbon atoms.    Examples of alkyl include methyl, ethyl, n- and i-propyl and n-, i-    and t-butyl. The heterocyclic ring contains 5 to 7, preferably 5 or    6 ring members.

Examples of the heterocyclic ring include pyrrolidine, piperidine,thiazolidine, piperazine, imidazolidine, hexamethyleneimine,hexahydro-1,3,5-triazine, morpholine, which may optionally besubstituted, preferably by methyl.

Most preferred are compounds of the general formulae (I) and (Ib)

in which

-   n represents 1 or 2,-   Subst. represents one of the abovementioned substituents, in    particular halogen, especially chlorine,-   A and Z have the abovementioned preferred meanings,-   Specifically, the following compounds may be mentioned:    Fungicides in the novel compositions for the control of plant pests    are for example:-   (1) Azole derivatives of the formula-   (2) Azole derivatives of the formula-   (3) The azole derivative of the formula-   (4) The compound    S_(x)  (V)-   (5) Azole derivative of the formula-   (6) Heterocycles of the formula    -   (VII-1) X═0, R⁸═CH₃, R⁹═H, R¹⁰═C₁₀H₂₁        -   (TRIDEMORPH)    -   (VII-2) X═0, R⁸═CH₃, R⁹═H, R¹⁰═C₉H₁₉        -   (ALDIMORPH)-   (7) Compound of the formula-   (8) Compound of the formula-   9) Compound of the formula-   (10) Compound of the formula-   (11) Compound of the formula-   (12) Compound of the formula-   (13) Compounds of the formula-   (14) Compounds of the formula    -   (XV-1) R¹²═CH₃        -   (PYRIMETHANIL)    -   (XV-2) R¹²═C≡C—CH₃        -   (MEPANIPYRIM)-   (15) Compounds of the formula    -   (XVI-1) R¹³═H        -   (DICHLORFLUANID)    -   (XVI-2) R¹³═CH₃        -   (TOLYLFLUANID)-   (16) Compound of the formula-   (17) Compound of the formula-   (18) Compound of the formula-   (19) Compound of the formula-   (20) Compound of the formula-   (21) Compound of the formula-   (22) Compound of the formula-   (23) Compound of the formula-   (24) Compounds of the formula     Cl₃C—S—R¹⁴  (XXV)-   (25) Compound of the formula-   (26) Compound of the formula-   (27) Compound of the formula-   (28) Compound of the formula-   (29) Compound of the formula-   (30) Compound of the formula-   (31) Compound of the formula-   (32) Compounds of the formula    -   (XXXIII-1) M═Mn        -   (ZINEB)    -   (XXXIII-2) M═Mn        -   (MANEB)    -   (XXXIII-3) M═Mn/Zn (Mancozeb)-   (33) Compound of the formula-   (34) Compound of the formula-   (35) Compound of the formula-   (36) Compound of the formula-   (37) Compound of the formula-   (38) Compounds of the formula    -   in which    -   R¹⁵ and R¹⁶, independently of each other, represent hydrogen,        halogen, methyl or phenyl, and    -   R¹⁷ represents hydrogen or methyl,-   (39)    8-′Butyl-2-(N-ethyl-N-n-propylamino)-methyl-1,4-dioxaspiro[4.5]decane    of the formula-   (40) Compound of the formula-   (41) Compound of the formula-   (42) Compound of the formula-   (43) Compound of the formula-   (44) Benzimidazole of the formula    -   R⁹=CONHtBu; R⁶=—NHCOOMe Benomyl    -   R⁹=H; R⁶=—NHCOOMe Carbendazin-   (45) Compound of the formula-   (46) Compound of the formula-   (47) Compound of the formula

The active compounds of the formula (I) are known for example from EP-OS(European Published Specification) 192 060.

The fungicidal active compounds are also known.

In the following publications, for example, there are described:

-   (1) Compounds of the formula (II)    -   DE-OS (German Published Specification) 2 201 063    -   DE-OS (German Published Specification) 2 324 010    -   DE-OS (German Published Specification) 2 737 489    -   DE-OS (German Published Specification) 3 018 866    -   DE-OS (German Published Specification) 2 551 560    -   EP 47 594    -   DE 2 735 872-   (2) Compound of the formula (III)    -   EP 68 813    -   U.S. Pat. No. 4,496,551-   (3) Compound of the formula (IV)    -   DE-OS (German Published Specification) 2 429 523    -   DE-OS (German Published Specification) 2 856 974    -   U.S. Pat. No. 4,108,411-   (6) Compounds of the formula (VII)    -   DL 140 041-   (7) Compound of the formula (VIII)    -   EP 382 375-   (8) Compound of the formula (IX)    -   EP 515 901-   (9) Compound of the formula (X)    -   EP 314 422-   (10) Compound of the formula (XI)    -   EP 49 854-   (11) Compound of the formula (XII)    -   DE-OS (German Published Specification) 1 770 288    -   U.S. Pat. No. 3,869,456-   (13) Compounds of the formula (XIV)    -   DE 2 207 576    -   U.S. Pat. No. 3,903,090    -   U.S. Pat. No. 3,755,350    -   U.S. Pat. No. 3,823,240-   (14) Compounds of the formula (XV)    -   EP 270 111-   (19) Compound of the formula (XX)    -   EP 219 756-   (34) Compound of the formula (XXXV)    -   U.S. Pat. No. 4,512,989-   (38) Compounds of the formula (XXXIX)    -   EP 398 692

Compounds of groups (15), (16), (17), (18), (23), (34), (25), (28),(31), (32), (33) and (38) to (47) are described for example in K. H.Büichel, “Pflanzenschutz und Schädlingsbekämpfung [Crop protection andpest control]”, pages 121-153, Georg Thieme-Verlag, Stuttgart, 1977. Thecompound of group (39) is known from EP-OS (European PublishedSpecification) 281 842.

Besides the active compound of the formula (I), the active compoundcombinations according to the invention contain at least one fungicidalactive compound, selected for example from the compounds of groups (1)to (47). Additionally, they may also contain other active compounds andalso customary auxiliaries and additives and diluents.

A synergistic effect is particularly apparent when the active compoundsin the active compound combinations according to the invention arepresent in particular weight ratios. However, the weight ratios of theactive compounds in the active compound combinations can be variedwithin a relatively wide range. In general

0.1 to 10 parts by weight, preferably

0.3 to 3 parts by weight, of at least one fungicidal active compoundfrom the groups (1) to (48) is/are allocated to one part by weight ofactive compound of the formula (I).

The combinations of active compounds according to the invention possessvery good fungicidal properties. They can be employed, in particular,for controlling phytopathogenic fungi, such as Plasmodiophoromycetes,Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes,Deuteromycetes etc.

The active compound combinations according to the invention areparticularly suitable for controlling cereal diseases, such as Erysiphe,Cochliobolus, Septoria, Pyrenophora and Leptosphaeria, and for useagainst fungal infestations of vegetables, grapes and fruit, for exampleagainst Venturia or Podosphaera on apples, Uncinula on vine plants orSphaeroteca on cucumbers.

The active compound combinations are also suitable for controllinganimal pests, preferably anthropods, in particular insects encounteredin agriculture, in forestry, in the protection of stored products and ofmaterials, and in the hygiene field. They are active against normallysensitive and resistant species and against all or some stages ofdevelopment. The abovementioned pests include:

From the order of the Isopoda, for example, Oniscus asellus,Armadillidium vulgare and Porcellio scaber.

From the order of the Diplopoda, for example, Blaniulus guttulatus.

From the order of the Chilopoda, for example, Geophilus carpophagus andScutigera spec.

From the order of the Symphyla, for example, Scutigerella immaculata.

From the order of the Thysanura, for example, Lepisma saccharina.

From the order of the Collembola, for example, Onychiurus armatus.

From the order of the Orthoptera, for example, Blatta orientalis,Periplaneta americana, Leucophaea maderae, Blattella germanica, Achetadomesticus, Gryllotalpa spp., Locusta migratoria migratorioides,Melanoplus differentialis and Schistocerca gregaria.

From the order of the Dermaptera, for example, Forficula auricularia.

From the order of the Isoptera, for example, Reticulitermes spp.

From the order of the Anoplura, for example, Pediculus humanus corporis,Haematopinus spp. and Linognathus spp.

From the order of the Mallophaga, for example, Trichodectes spp. andDamalinea spp.

From the order of the Thysanoptera, for example, Hercinothrips femoralisand Thrips tabaci.

From the order of the Heteroptera, for example, Eurygaster spp.,Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodniusprolixus and Triatoma spp.

From the order of the Homoptera, for example, Aleurodes brassicae,Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicorynebrassicae, Cryptomyzus ribis, Doralis fabae, Doralis pomi, Eriosomalanigerum, Hyalopterus arundinis, Macrosiphum avenae, Myzus spp.,Phorodon humuli, Rhopalosiphum padi, Phylloxera vastrix, Pemphigus spp.,Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, Lecaniumcorni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens,Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp. and Psyllaspp.

From the order of the Lepidoptera, for example, Pectinophoragossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletisblancardella, Hyponomeuta padella, Plutella maculipennis, Malacosomaneustria, Euproctis chrysorrhoea, Lymantria spp. Bucculatrixthurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltiaspp., Earias insulana, Heliothis spp., Laphygma exigua, Mamestrabrassicae, Panolis flammea, Prodenia litura, Spodoptera spp.,Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyraustanubilalis, Ephestia kuehniella, Galleria mellonella, Tineolabisselliella, Tinea pellionella, Hofinannophila pseudospretella,Cacoecia podana, Capua reticulana, Choristoneura fumiferana, Clysiaambiguella, Homona magnanima and Tortrix viridana.

From the order of the Coleoptera, for example, Anobium punctatum,Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus,Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedoncochleariae, Diabrotica spp., Psylliodes chrysocephala, Epilachnavarivestis, Atomaria spp., Oryzaephilus surinamensis, Anthonomus spp.,Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus,Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogodermaspp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus,Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp.,Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha,Amphimallon soistitialis and Costelytra zealandica.

From the order of the Hymenoptera, for example, Diprion spp., Hoplocampaspp., Lasius spp., Monomorium pharaonis and Vespa spp.

From the order of the Diptera, for example, Aedes spp., Anopheles spp.,Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphoraerythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp.,Gastrophilus spp., Hyppobosca spp., Stomoxys spp., Oestrus spp.,Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinellafrit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleaeand Tipula paludosa.

The fact that the active compound combinations are well tolerated byplants at the concentrations required for controlling plant diseasespermits a treatment of aerial parts of plants, of propagation stock andseeds, and of the soil.

The active compounds of the invention can be converted to the customaryformulations, such as solutions, emulsions, suspensions, powders, foams,pastes, granules, aerosols, very fine capsules in polymeric substancesand in coating compositions for seed, as well as ULV formulations.

These formulations are produced in a known manner, for example by mixingthe active compounds with extenders, that is, liquid solvents, liquefiedgases under pressure, and/or solid carriers, optionally with the use ofsurface-active agents, that is emulsifying agents and/or dispersingagents, and/or foam-forming agents. In the case of the use of water asan extender, organic solvents can, for example, also be used asauxiliary solvents. As liquid solvents, there are suitable in the main:aromatics, such as xylene, toluene or alkylnaphthalenes, chlorinatedaromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes,chloroethylenes or methylene chloride, aliphatic hydrocarbons, such ascyclohexane or paraffins, for example mineral oil fractions, alcohols,such as butanol or glycol as well as their ethers and esters, ketones,such as acetone, methyl ethyl ketone, methyl isobutyl ketone orcyclohexanone, strongly polar solvents, such as dimethylformamide anddimethyl sulphoxide, as well as water; by liquefied gaseous extenders orcarriers are meant liquids which are gaseous at ambient temperature andunder atmospheric pressure, for example aerosol propellants, such ashalogenated hydrocarbons as well as butane, propane, nitrogen and carbondioxide; as solid carriers there are suitable: for example groundnatural minerals, such as kaolins, clays, talc, chalk, quartz,attapulgite, montmorillonite or diatomaceous earth, and ground syntheticminerals, such as highly disperse silica, alumina and silicates; assolid carriers for granules there are suitable: for example crushed andfractionated natural rocks such as calcite, marble, pumice, sepioliteand dolomite, as well as synthetic granules of inorganic and organicmeals, and granules of organic material such as sawdust, coconut shells,maize cobs and tobacco stalks; as emulsifying and/or foam-forming agentsthere are suitable: for example non-ionic and anionic emulsifiers, suchas polyoxyethylene fatty acid esters, polyoxyethylene fatty alcoholethers, for example alkylaryl polyglycol ethers, alkylsulphonates, alkylsulphates, arylsulphonates as well as albumen hydrolysis products; asdispersing agents there are suitable: for example lignin-sulphite wasteliquors and methylcellulose.

Adhesives such as carboxymethylcellulose and natural and syntheticpolymers in the form of powders, granules or latices, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, as well as naturalphospholipids, such as cephalins and lecithins, and syntheticphospholipids, can be used in the formulations. Other additives can bemineral and vegetable oils.

It is possible to use colorants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian Blue, and organic dyestuffs,such as alizarin dyestuffs, azo dyestuffs and metal phthalocyaninedyestuffs, and trace nutrients such as salts of iron, manganese, boron,copper, cobalt, molybdenum and zinc.

The formulations in general contain between 0.1 and 95 per cent byweight of active compound, preferably between 0.5 and 90%.

The active compound combinations according to the invention can bepresent in the formulations as mixtures with other known activecompounds, such as fungicides, insecticides, acaricides and herbicides,and also as mixtures with fertilizers or plant growth regulators.

The active compound combinations can be used as such, in the form oftheir formulations or as the use forms prepared therefrom, such asready-to-use solutions, emulsifiable concentrates, emulsions,suspensions, wettable powders, soluble powders and granules.

They are used in the customary manner, for example by watering,spraying, atomizing, scattering, brushing on and as a powder for dryseed treatment, a solution for seed treatment, a water-soluble powderfor seed treatment, a water-soluble powder for slurry treatment, or byencrusting.

In the treatment of parts of plants, the concentrations of activecompound in the use forms can be varied within a substantial range. Ingeneral, they are between 1 and 0.0001% by weight, preferably between0.5 and 0.001%.

In the treatment of seed, amounts of 0.001 to 50 g of active compoundper kilogram of seed are generally required, preferably 0.01 to 10 g.

In the treatment of the soil, active compound concentrations from0.00001 to 0.1% by weight, preferably 0.0001 to 0.02% by weight, arerequired at the site of action.

The good fungicidal activity of the active compound combinationsaccording to the invention can be seen from the examples which follow.While the individual active compounds or the known active compoundcombinations show weaknesses with regard to the fungicidal activity, thetables of the examples which follow show clearly that the activity foundin the case of the active compound combinations according to theinvention exceeds the total of the activities of individual activecompounds and also exceeds the activities of the known active compoundcombinations.

In the examples that follow, imidacloprid is employed as active compoundof the formula (I). The fungicidal active compounds also used are statedin the examples.

EXAMPLE A Drechslera Graminea Test (barley)/Seed Treatment (syn.Helminthosporium Gramineum)

The active compounds are used as a powder for dry seed treatment. Theyare prepared by extending the active compound in question with rock mealto give a finely pulverulent mixture which ensures uniform distributionon the seed surface.

To carry out the seed treatment, the infected seed and the seed-dressingproduct are shaken for 3 minutes in a sealed glass flask.

The seed, embedded in screened, moist standard soil in sealed Petridishes, is exposed to a temperature of 4° C., for 10 days in arefrigerator. This triggers germination of the barley and, ifappropriate, of the fungal spores. 2×50 pregerminated barley kernels aresubsequently sown in standard soil at a depth of 3 cm and grown in agreenhouse at a temperature of approximately 18° C. in seed boxes whichare exposed to the light for 15 hours per day.

Approximately 3 weeks after sowing, the plants are evaluated forsymptoms of barley leaf stripe.

Mixtures of imidacloprid with tebuconazole, captan, euparen M,bitertanol, triazoxide, thiram, fludioxonil exhibit a pronouncedincrease in activity as compared with treatment using the individualcompounds.

EXAMPLE B Fusarium Nivale Test (wheat)/Seed Treatment

The active compounds are used as a powder for dry seed treatment. Theyare prepared by extending the active compound in question with rock mealto give a finely pulverulent mixture which ensures uniform distributionon the seed surface.

To carry out the seed treatment, the infected seed and the seed-dressingproduct are shaken for 3 minutes in a sealed glass flask.

2×100 wheat kernels are subsequently sown in standard soil at a depth of1 cm and grown in the greenhouse at a temperature of approximately 10°and a relative atmospheric humidity of approximately 95% in seed boxeswhich are exposed to the light for 15 hours per day.

Approximately 3 weeks after sowing, the plants are evaluated for snowblight symptoms.

Mixtures of imidacloprid with euparen, guazatine, triadimenol,difenconazole, fenpiclonil exhibit a pronounced increase in activity ascompared with treatment using the individual compounds.

EXAMPLE C

Phaedon Larvae Test

Solvent: 7 parts by weight of dimethylformamide Emulsifier: 1 part byweight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent and thestated amount of emulsifier, and the concentrate is diluted with waterto the desired concentration.

Cabbage leaves (Brassica oleracea) are treated by being dipped into thepreparation of the active compound of the desired concentration and areinfested with mustard beetle larvae (Phaedon cochleariae), as long asthe leaves are still moist.

After 7 days the destruction in % is determined.

Mixtures of imidacloprid with anilazine, benomyl, bitertanol, captan,diclofluanid, mancozeb, maneb, metalaxyl, prochloraz, procymidone,sulphate, tolylfluanid, triadimefon, triadimenol exhibit a pronouncedincrease in activity as compared with treatment using the individualcompounds.

EXAMPLE D

Myzus Test

Solvent: 7 parts by weight of dimethylformamide Emulsifier: 1 part byweight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent and thestated amount of emulsifier, and the concentrate is diluted with waterto the desired concentration.

Cabbage leaves (Brassica oleracea) heavily infested with aphids (Myzuspersicae) are treated by dipping in the preparation of active compoundof the desired concentration.

After 6 days, the destruction in % is determined.

Mixtures of imidacloprid with bitertanol, fenpropimorph, prochloraz,tebuconazole exhibit a pronounced increase in activity as compared withtreatment using the individual compounds.

EXAMPLE E

Botrytis Test (Beans)/Protective

Solvent: 4.7 parts by weight of acetone Emulsifier: 0.3 parts by weightof alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent and thestated amount of emulsifier, and the concentrate is diluted with waterto the desired concentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound until dripping wet. After the spraycoating has dried on, two small pieces of agar covered with Botrytiscinerea are placed on each leaf. The inoculated plants are placed in adarkened humid chamber at 20° C. 3 days after the inoculation, the sizeof the infected spots on the leaves is evaluated.

Mixtures of imidacloprid with procymidone, tolyfluanid, tebuconazoleexhibit a pronounced increase in activity as compared with treatmentusing the individual compounds.

EXAMPLE F

Podosphaera Test (apple)/Protective

Solvent: 4.7 parts by weight of acetone Emulsifier: 0.3 parts by weightof alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound until dripping wet. After the spraycoating has dried on, the plants are inoculated by dusting with conidiaof the causative organism of apple mildew (Podosphaera leucotricha).

The plants are then placed in a greenhouse at 23° C. and a relativeatmospheric humidity of about 70%.

Evaluation is carried out 10 days after the inoculation.

Mixtures of imidacloprid with fenpropidin, triadimenol exhibit aprounced increase in activity as compared with treatment using theindividual compounds.

1. A composition comprising synergistic amounts of a compound of theformula (I)

wherein X represents ═N—, E represents an electron-withdrawing radical,R represents optionally substituted hetarylalkyl, A represents hydrogenor alkyl, Z represents alkyl, —NH-alkyl, —N(alkyl)₂, or A and Z togetherwith the atoms to which they are bonded, form a saturated or unsaturatedheterocyclic ring, and at least one fungicidal active compoundcomprising azoxystrobin, excluding cyclopropylcarboxamides andazolylmethylcycloalkanes, wherein the combination of imidacloprid and atleast one fungicidal active compound selected from the group consistingof tebuconazole, compounds of the formula

and the compound of formula (XXXVIII)

is excluded.
 2. The composition of claim 1, comprising about 0.1 toabout 10 parts by weight of said at least one fungicidal active compoundper part by weight of the compound of the formula (I).
 3. Thecomposition of claim 1, comprising about 0.3 to about 3 parts by weightof said at least one fungicidal active compound per part by weight ofthe compound of the formula (I).
 4. The composition of claim 1, whereinX represents ═N—, E represents NO₂ or CN, R represents hetarylmethyl orhetarylethyl having up to 6 ring atoms and having N, O or S asheteroatoms; A represents hydrogen or C₁-C₄-alkyl, and Z representsC₁-C₄-alkyl, —NH(C₁-C₄-alkyl), —N(C₁-C₄-alkyl)₂, or A and Z togetherwith the atoms to which they are bonded form a saturated or unsaturatedheterocyclic ring comprising 0, 1 or 2 heteroatoms and/or heterogroups.5. The composition of claim 1, wherein R represents thienyl, furyl,thiazolyl, imidazolyl or pyridyl, each of which may be unsubstituted orsubstituted with substituents selected from the group consisting ofC₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkyl and 1 to 5halogen atoms, hydroxyl, halogen, cyano, nitro, amino, and monoalkyl-and dialkylamino having 1 to 4 carbon atoms per alkyl group.
 6. Thecomposition of claim 1, wherein A and Z together with the atoms to whichthey are bonded form an unsubstituted or substituted ring group selectedfrom pyrrolidine, piperidine, thiazolidine, piperazine, imidazolidine,hexamethyleneimine, hexahydro-1,3,5-triazine or morpholine.
 7. Thecomposition of claim 1, wherein the compound of formula (I) comprisesimidacloprid and said at least one fungicidal active compound is acompound of the formula (VIII)


8. A process for preparing the composition of claim 1 comprising mixingthe compound of formula (I) and said at least one fungicidal activecompound with at least one of the extenders and surface-activesubstances.
 9. A process for controlling at least one of fungi andinsects comprising applying synergistic amounts of the composition ofclaim 1 to at least one of fungi, insects, fungi locus, and insect locusso that the composition is applied at a concentration sufficient forcontrolling at least one plant disease.
 10. The process of claim 9,wherein the step of applying comprises treating seed with from about0.001 to about 50 g of the composition per kilogram of seed.
 11. Theprocess of claim 9, wherein the step of applying comprises treating soilwith from about 0.00001 to about 0.1% by weight of the composition. 12.The process of claim 9, wherein the weight ratio of the compound offormula (I) to said at least one fungicidal active compound is fromabout 1:0.1 to about 1:10.
 13. The composition of claim 7 wherein saidat least one fungicidal active compound is said compound of the formula(VIII)


14. The composition of claim 1, wherein the compound of formula (I) isimidacloprid.